Fluorinated amphiphiles are an important class of compounds because of their tendency to self-assemble into nanostructures such as monolayers, micelles, or vesicles, in a fashion distinct from their hydrocarbon-based counterparts. Particularly, amine and guanidine-terminated molecules in this class can potentially decorate phosphate-rich biomolecules through selective non-covalent interactions such as hydrogen bonding.
While syntheses of several highly fluorinated amphiphiles or surfactants have been reported, amine- and guanidine-functionalized fluorocarbons remain largely under-addressed despite the potential synthetic utility of nitrogen-containing groups as functionalization handles and biochemical tools. The known synthetic routes to highly fluorinated amines have drawbacks: for example, highly fluorinated amines can be prepared from routes such as fluoroalkylation of ammonia with an alkyl chloride, hydrogenation of fluoro-organic azides, and the Gabriel synthesis, with the latter two involving high-temperature displacement of fluoroalkyl tosylates. These methods are of limited scope or involve harsh conditions incompatible with some biologically relevant substrates.
Accordingly, there is a need for improved methods of making amphiphiles that are useful for biochemical applications.